Thomas Smith was an artist, sailor, and slave trader in colonial New England. Smith is best known for the self-portrait he painted around 1680, which, according to the Worcester Art Museum, is "the only seventeenth-century New England portrait by an identified artist and the earliest surviving American self-portrait." Smith was also a prominent Boston merchant and slave trader who participated in the enslavement of Native Americans during King Philip's War.
Smith's style exhibits similarities with the painting styles of the English and Dutch Golden Ages, particularly evident in his skillful use of light and shadow to create an expressive effect. The subject of the portrait is seated on a chair with maroon upholstery adorned with studs. Smith is dressed in a typical Puritan dark coat and wears a lace jabot, which was characteristic of the period. In the top-right corner, a maroon curtain with a golden tassel adds a sense of depth to the composition.

Notably, the portrait features a window in the top-left corner depicting a naval battle between Dutch and English forces, engaged with an unidentified adversary. Below them, a fortification is depicted, flying two red flags, one of which bears three white crescents. This detail may allude to a significant event or aspect of Smith's career.